62 pages 2-hour read

Careless People

Nonfiction | Autobiography / Memoir | Adult | Published in 2025

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Chapters 24-32Chapter Summaries & Analyses

Chapter 24 Summary: “California Time”

Content Warning: This section of the guide includes discussion of illness and sexual harassment.


Wynn-Williams was subtly persuaded to move to Silicon Valley. While no one from the policy team was based in California, Silicon Valley was becoming the “place political power players ha[d] to visit” (189).

Chapter 25 Summary: “Muppets and Monsignors”

In September 2015, President Xi of China visited Seattle, Washington, where Amazon and Microsoft are headquartered, and skipped Silicon Valley. Zuckerberg was not invited to a “closed-door meeting with thirty American and Chinese CEOs” (192). Instead, he had a very brief meeting with Xi. When posting a photo of that meeting, Zuckerberg offended China because only the back of President Xi’s head is showing.


The next day, September 26, Zuckerberg addressed the United Nations (UN), hoping to build support for Internet.org. Zuckerberg refused to speak in the morning and therefore took a less important slot in the afternoon. Facebook was attempting to include references to connectivity in the UN’s Sustainable Development Goals.


At lunch, Zuckerberg sat next to Angela Merkel, the German chancellor. Merkel pressed him “to remove antirefugee posts from Facebook in Germany” (196), where there were “several open investigations into Facebook privacy issues” (195). Shockingly, when he got on stage to deliver his address, Zuckerberg announced that Facebook planned to bring the Internet to refugee camps, although they had no plans to do so. Later, it became apparent this would not happen, causing the author to observe that Zuckerberg did not care and said things simply because they sounded good. With the Pope in town, Zuckerberg requested and was denied a meeting.


Zuckerberg attended the Global Citizen Festival in Central Park in New York. Once again, there were scheduling issues, particularly with Big Bird. Zuckerberg’s assistant suggested that a video be made in place of an appearance. When Zuckerberg gave his in-person address, the video was mistakenly playing over him. He looked like “an animal in a trap” (199). Afterward, Wynn-Williams apologized, but he told her that she had done an amazing job. Wynn-Williams comments, “[I]t’s the most human he’s ever seemed” (200).

Chapter 26 Summary: “The Wicked Witch of the West”

With 67 digital rights groups opposing Internet.org, there was pressure to change the name or brand. Wynn-Williams explains that “Internet.org entrenches the digital divide between the haves and the have-nots, by delivering a crap version of the internet to two-thirds of the world” (203). Chris Daniels, who ran Internet.org, called a meeting in a room with the title the “Wicked Witch of the West” (203). Zuckerberg refused to change the name anywhere except in Brazil, where it would be called Free Basics. In another month, it would be called that everywhere.

Chapter 27 Summary: “Street Fighter Tactics”

In August 2015, Zuckerberg called a meeting of all those working on Free Basics to instruct the team to employ “street fighter tactics” like Uber did (207). He wanted protests and a list of adversaries. Adversaries included anyone who opposed Facebook, which was “basically everyone” when it came to Free Basics (208). Arguing that Zuckerberg was about to destroy relationships with governments around the world, Wynn-Williams marks this as a turning point. Henceforth, she would fulfill Zuckerberg’s orders half-heartedly.


India became a special target given the size of the unconnected population. Facebook spent tens of millions of dollars to build the appearance of popular support. They promised free T-shirts to get people to protest. The Indian regulator had asked the public to comment on questions that would determine the fate of Free Basics. Zuckerberg had the team create a large button to prompt Indian Facebook users to contact the regulator, which, when clicked, sent a form letter. The click additionally notified the user’s friends. As a result, there were almost 17 million submissions sent to the regulator by January 2016. However, the regulator only received 1.4 million, as a “technical glitch” prevented the bulk of the emails from being sent (211).


Although Facebook convinced the regulator to accept all 17 million comments, in February 2016, the regulator banned Free Basics. Wynn-Williams comments, “We’[d] never lost a fight this big” (212). The other two priority projects of Internet.org crashed and burned soon thereafter. The drone that was supposed to deliver Wi-Fi crashed during a test flight, and SpaceX exploded on a launchpad, destroying the Internet.org satellite.

Chapter 28 Summary: “Lean In and Lie Back”

Although Wynn-Williams was in the final stages of pregnancy, Sandberg insisted that she accompany her to the World Economic Forum in Davos, Switzerland. Given the terrorist attacks in Paris in 2015, governments were less interested in privacy and more in surveillance, to Facebook’s delight. More importantly, Wynn-Williams noticed a “changing power dynamic” (217), as politicians were seeking Facebook’s support in elections and not pushing regulations.


While flying back from Davos, Sandberg asked Wynn-Williams to come to bed with her. Wynn-Williams refused, causing something to break between them. Sandberg played favorites and rewarded those closest to her. Once back in California, Sandberg invited her new associate, Sadie, to her house for dinner and a sleepover.

Chapter 29 Summary: “Citizen Sanchez”

Wynn-Williams needed to secure American citizenship and was about to take the exam. In an email, Kaplan asked her if she got the “dirty Sanchez” question (223). After googling it, she felt uncomfortable. This was “a new low” for Kaplan but not the first time he had said something inappropriate to her (223).


Although Wynn-Williams aced the exam, she had to start the citizenship process over again because she had not lived in California long enough. Facebook’s lawyers missed this and had to apply to rush her petition. Otherwise, her partner Tom’s visa would expire and they would have to leave the US. As a result, she could not leave her job at Facebook.

Chapter 30 Summary: “Poker Face”

In February 2016, governmental leaders were worried about the proliferation of hate speech and radicalization of terrorists on Facebook. They were looking for ways to tax the company.


A board meeting was called to address these concerns. Since Zuckerberg and Sandberg controlled the board, the atmosphere was relaxed. Instead of being frightened by Wynn-Williams’s presentation, the board asked what deals could be made. Days later at her performance review, Kaplan chastised Wynn-Williams for not always having a “poker face.” She rolled her eyes when a board member suggested that Facebook get closer to right-wing political parties, for example. Otherwise, Kaplan said, “great review” (229).

Chapter 31 Summary: “A Heartwarming Story”

Since WhatsApp, which is owned by Facebook, refused to disclose messages in a Brazilian drug-trafficking case, Diego Dzodan, a Facebook vice president, was arrested in March 2016. Zuckerberg was more concerned about his Facebook post on the matter than with getting his employee out of jail. His advisors, including Wynn-Williams and Schrage, explained that his post would make it more difficult to get Dzodan out of jail, as it would destroy the argument that WhatsApp was a different company from Facebook and aggravate law enforcement.


While an appeals court released Dzodan, Wynn-Williams comments that Zuckerberg could not have been “more disappointing” (234). He was not worried about Dzodan, obsessed over “some stupid post” (235), and then went to dinner. She concluded that she needed to leave Facebook.

Chapter 32 Summary: “What to Not Expect When You’re Expecting”

Wynn-Williams realized that she traveled to the epicenter of the Zika virus outbreak when she was pregnant. Begrudgingly, her doctor ordered an ultrasound at her request, which showed no problems.


In March 2016, she delivered a healthy baby girl but began to convulse and lost large amounts of blood afterward. She was taken to another hospital, where she underwent surgery and was placed on life support in intensive care. There, she was relieved to see Tom, who told her that he named the baby Xanthe while she was in a coma. Wynn-Williams learned that she had an “amniotic fluid embolism” (244), as something entered her bloodstream and stopped it from clotting. Once home, she continued to bleed and was unable to walk. This near-death experience increased her resolve to leave Facebook.

Chapters 24-32 Analysis

The Influence of Technology on Politics and People’s Lives is not necessarily always positive, as Wynn-Williams began to see while she was at Facebook. In recounting the Board of Directors meeting over government concerns about terrorism and radicalization on Facebook, Wynn-Williams stresses that there was no real plan at the company to confront the problem. Instead, she observed that at least one board member suggested that Facebook deliberately cultivate closer ties to right-wing political parties. In recounting this meeting, Wynn-Williams’s account suggests that there were two growing problems with Facebook’s political influence: First, it did not care about addressing problematic uses of the platform, even in the case of terrorism; and second, the company was becoming more partisan as to which types of politicians and parties they would favor, and Wynn-Williams discovered that they were not of a progressive variety.   


Most significantly, the power dynamics between Facebook and foreign governments were changing in general, as politicians increasingly relied on the platform for electoral success. Thus, many governments were also more and more reluctant to challenge Facebook to pay taxes or operate in the public interest. In this way, Facebook had started to become more powerful than national democratic governments, yet the company answered only to its shareholders, not citizens. There were therefore fewer avenues for checking the company’s greed or holding it accountable.


The push to get countries to accept Internet.org showcases The Problem of Corporate Greed. The product was a poor one, which would amplify the divide between the digital haves and have-nots. Zuckerberg’s insistence on using “dirty” tactics to ensure that it was not banned in India and elsewhere resulted in a manipulated mass-letter campaign. Technical features were used to encourage people not only to submit pre-written letters to the regulator in India but also to notify their “friends” about their letters without their knowledge. While India ultimately blocked the software, Zuckerberg’s attempt to manipulate public opinion and directly interfere in the decision-making process of a foreign country demonstrate both the company’s greed and Zuckerberg’s increasing arrogant attitude toward democratic governments.


Wynn-Williams’s characterization of Zuckerberg continues to emphasize his personal arrogance and unsuitability for power. He offended President Xi of China when he posted a picture showing the back of his head. Later, he lied about Facebook’s initiative to ensure connectivity in refugee camps. There was no such initiative at Facebook, and it was not feasible to have one. He made the comment to counteract the criticisms of Chancellor Merkel of Germany, not caring that a lack of follow-through would harm relations in the future.


Wynn-Williams documents her harassment by those to whom she reported at Facebook, reflecting Gender and Power Dynamics in High-Tech Industries. She was sexually harassed when Sandberg asked her to accompany her to bed on a plane ride. When she refused, Sandberg treated her differently. Similarly, Kaplan, who said inappropriate things to her, invited her to look up the “dirty Sanchez” question right before she took her citizenship test. “Dirty Sanchez” is a vulgar term that refers to drawing a mustache on the face of someone with a penis after anal sex. Wynn-Williams was horrified when she learned this.


Management’s disregard for the welfare of its employees also extended beyond gender. When a male employee was arrested in Brazil, Zuckerberg not only did nothing to get him released but also jeopardized the employee’s defense with his insistence on a Facebook post. He was not worried about Dzodan and went out to dinner before the employee was released. In recounting these incidents, Wynn-Williams exposes how the unprofessional hierarchy at Facebook resulted in the abuse and neglect of lower-ranking employees.

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